Electrochiroptical response of 2,2′-(2,2-diarylethenyl)binaphthyl-type electron donors that undergo reversible C-C bond formation/breaking upon two-electron transfer

Hiroki Higuchi, Eisuke Ohta, Hidetoshi Kawai, Kenshu Fujiwara, Takashi Tsuji, Takanori Suzuki

Research output: Contribution to journalArticle

47 Citations (Scopus)

Abstract

2,2′-[2,2-Bis(4-dimethylaminophenyl)ethenyl]biphenyl (1) is a strong electron donor that undergoes oxidative C-C bond formation to give a stable dication rac-2 2+ , the 9,10-dihydrophenanthrene derivative substituted with two bis(4-dimethylaminophenyl)methylium chromophores. This dication salt regenerates the starting diolefin 1 by reductive C-C bond breaking, thus realizing a new electrochromic system with high electrochemical bistability and a vivid change in color from yellow to deep blue. Similarly, the binaphthylic diolefin rac-3 and the helicene-type dication rac-4 2+ are interconvertible upon two-electron transfer. Both the UV-vis and CD spectra changed drastically upon electrochemical transformation between optically pure 3 and 4 2+ , which represents a new electrochiroptical system.

Original languageEnglish
Pages (from-to)6605-6610
Number of pages6
JournalJournal of Organic Chemistry
Volume68
Issue number17
DOIs
Publication statusPublished - Sep 1 2003

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Alkadienes
Electrons
Chromophores
Salts
Color
Derivatives

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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Electrochiroptical response of 2,2′-(2,2-diarylethenyl)binaphthyl-type electron donors that undergo reversible C-C bond formation/breaking upon two-electron transfer. / Higuchi, Hiroki; Ohta, Eisuke; Kawai, Hidetoshi; Fujiwara, Kenshu; Tsuji, Takashi; Suzuki, Takanori.

In: Journal of Organic Chemistry, Vol. 68, No. 17, 01.09.2003, p. 6605-6610.

Research output: Contribution to journalArticle

Higuchi, Hiroki ; Ohta, Eisuke ; Kawai, Hidetoshi ; Fujiwara, Kenshu ; Tsuji, Takashi ; Suzuki, Takanori. / Electrochiroptical response of 2,2′-(2,2-diarylethenyl)binaphthyl-type electron donors that undergo reversible C-C bond formation/breaking upon two-electron transfer. In: Journal of Organic Chemistry. 2003 ; Vol. 68, No. 17. pp. 6605-6610.
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abstract = "2,2′-[2,2-Bis(4-dimethylaminophenyl)ethenyl]biphenyl (1) is a strong electron donor that undergoes oxidative C-C bond formation to give a stable dication rac-2 2+ , the 9,10-dihydrophenanthrene derivative substituted with two bis(4-dimethylaminophenyl)methylium chromophores. This dication salt regenerates the starting diolefin 1 by reductive C-C bond breaking, thus realizing a new electrochromic system with high electrochemical bistability and a vivid change in color from yellow to deep blue. Similarly, the binaphthylic diolefin rac-3 and the helicene-type dication rac-4 2+ are interconvertible upon two-electron transfer. Both the UV-vis and CD spectra changed drastically upon electrochemical transformation between optically pure 3 and 4 2+ , which represents a new electrochiroptical system.",
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AU - Higuchi, Hiroki

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AU - Tsuji, Takashi

AU - Suzuki, Takanori

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N2 - 2,2′-[2,2-Bis(4-dimethylaminophenyl)ethenyl]biphenyl (1) is a strong electron donor that undergoes oxidative C-C bond formation to give a stable dication rac-2 2+ , the 9,10-dihydrophenanthrene derivative substituted with two bis(4-dimethylaminophenyl)methylium chromophores. This dication salt regenerates the starting diolefin 1 by reductive C-C bond breaking, thus realizing a new electrochromic system with high electrochemical bistability and a vivid change in color from yellow to deep blue. Similarly, the binaphthylic diolefin rac-3 and the helicene-type dication rac-4 2+ are interconvertible upon two-electron transfer. Both the UV-vis and CD spectra changed drastically upon electrochemical transformation between optically pure 3 and 4 2+ , which represents a new electrochiroptical system.

AB - 2,2′-[2,2-Bis(4-dimethylaminophenyl)ethenyl]biphenyl (1) is a strong electron donor that undergoes oxidative C-C bond formation to give a stable dication rac-2 2+ , the 9,10-dihydrophenanthrene derivative substituted with two bis(4-dimethylaminophenyl)methylium chromophores. This dication salt regenerates the starting diolefin 1 by reductive C-C bond breaking, thus realizing a new electrochromic system with high electrochemical bistability and a vivid change in color from yellow to deep blue. Similarly, the binaphthylic diolefin rac-3 and the helicene-type dication rac-4 2+ are interconvertible upon two-electron transfer. Both the UV-vis and CD spectra changed drastically upon electrochemical transformation between optically pure 3 and 4 2+ , which represents a new electrochiroptical system.

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